Dee Dee Ch 2

Part 2. My First Day

On Tuesday, I rushed home after school and told my mom I was going over to Mrs. D’Harley’s to start work. I said I was going to have a shower first and she asked me why I was going to do that before work rather than after. A good question I guess, because I got all flustered and didn’t know what to say. I guess I subconsciously thought I should be clean in case something happened when I was there although I knew that was stupid. But I remembered I thought I should jerk off again before I went so I wouldn’t get a hard-on when I saw her again. So I had a shower and yes, I jerked off in the shower thinking about what she looked like in the garters and what her breasts looked like when she bent over in front of me. I put on the tightest underwear I could find thinking it would hold my erection in so it wouldn’t show if I got one again.

When I rang the bell, she answered it right away and told me to come in, that she had been waiting for me. I couldn’t believe how she was dressed. The first thing I did was look at her feet, and sure enough, she was wearing some high heel shoes again, though this time they were bright white ones with open toes, little straps around her ankles and a little design with holes above her toes. The heels were quite high but I don’t think they were as high as the black shoes she was wearing the first time I saw her. She had on the shortest pair of cutoff denims that I have ever seen. They seemed to go right to her crotch. What really took my breath away though was that she was wearing black silk stockings that only went about half way up her thighs and they were held up by some garters that came out of her shorts. She was also wearing what looked like a man’s white shirt that only had one button done up, right in the middle. It was open all down her front and she was wearing another black bra, but this one was lacier and had a little strap holding the two cups together so I could see some of her tits again.

When she turned to lead me in, I could see the other pair of garter straps coming out of the back of her shorts. They circled around her bum and down to her stockings in the most erotic way. I noticed that the tops of her legs were a little bigger that I remember the last time, but they looked so neat in the stockings I couldn’t take my eyes off of them. Her shorts were so short that I could see just the edge of the tiniest panties I could imagine, right in the crack of her ass. They must have been thong type panties because I could hardly see any of them.

When she went to the couch across from where she motioned me to sit, she sat on the arm of it for some reason, rather than right on it. When she did, her legs straddled the arm and I could see all of her legs, and even her panties around the edges of her shorts. I am sure she knew I was looking at her legs but she didn’t seem to mind, in fact, she kept shifting and trying to get comfortable and every time she did, I could see more of her panties. I think I was turning red again and I could feel my cock getting hard and I was mad thinking that I masturbated for nothing. She looked even more beautiful than I remembered, though, even though she was as old as my mom was. I looked at her face and I could see some wrinkles under the makeup, but she was so neat looking. When I finally was able to take my eyes off her legs and her breasts, I also noticed she was wearing a black collar, sort of like a choker. I thought that it looked really neat.

She started to ask me questions about my interests and how I was doing at school and stuff. After a while, I said I should probably get started and she said not to worry, that she would pay me for the whole time I was here, even when I was only chatting with her. She said she lived alone and that she missed having company and asked me if I would mind chatting with her once in a while. I told her no and she said she was interested in young men and what they did and thought about and did I mind answering her questions. I told her no that was okay; that I would try to answer any type of questions she had. She kept shifting on the sofa and I kept staring at her legs and wondering how she ever managed to walk in shoes that had heels that high. I thought she was the most beautiful woman I had ever seen. I think I could have stayed there looking at her forever. I don’t remember if my cock was hard or not but it must have been. At least I was sitting so she couldn’t see it. Then she got up and shifted to sit right on the couch and when she did, she turned a little to the side I could see a little bit of the top of her tits. Earlier I thought I could see a little flower pattern in her panties and now I could see a pattern in her bra so I wondered if they were a matching set. I remember thinking how neat that was. We kept talking for a few more minutes.

Finally, she said I could start by cleaning the pool. She told me she was going to change into a swimsuit so that she could show me how to do it and that I should start by getting the equipment from the garage. I said sure and went out to do that. A little while later, I heard her call my name through the kitchen window. When I responded, she asked me if I could come in for a minute.

When I went into the house and I saw her, I couldn’t believe my luck. She had on a bikini and she had on another pair of high heel shoes. They were red and they had really high heels. She looked so neat. The bra part was quite wide and seemed to push her tits up and out and they looked so cool. It was a kind of red and pink or purple kind of material and it was wide where her tits were so that there was a lot of cleavage showing. A strap that went around the back of her neck held up the top and the bottom was not like a thong or anything but it was quite high on her hips and I could see all of her legs.

“Robby”, she said, “I just bought myself a new bathing suit and I wanted to know if you thought it fit me okay and looked good on me before I wore it outside. What do you think? Is it okay?” And with that, she started to turn around and pose in it so I could see it from different angles.

When she stood towards me and bent forward a bit, I could see almost all of her tits. And her legs looked so long and sexy in the high heels.

“Well”, she said, “what do you think? Does it look okay on me? I am such a poor judge of what looks good on me.”

“I think it looks great on you, Mrs. D’Harley,” I said. “Are you just saying that to make me feel good Robby, or do you really mean it?” “No, no, I think it looks great on you.” “That is sweet of you to say, Robby, thank you, you are so sweet.”

I don’t know if she noticed how red I must have been or if she noticed that I had a hard-on or not, but she just smiled, adjusted her tits in the bra part and said, “Okay, I’ll wear it. Let’s go and I’ll show you how to clean the pool.”

I followed her out, watching her walk in the heels and my hard-on got even bigger from looking at her bum and her legs. Somehow, I got myself under control and after a few moments, she told me I was getting the hang of it and I should be okay on my own. She said she was going to go into the pool to cool off while I finished.

After swimming a few laps, she got out and because her suit was wet, it hung lower on her hips and her tits and I could see them almost as clear as day because the fabric was wet. She went over to the diving board, which was right across from me. I was pretending not to notice her but I couldn’t keep my eyes off her, and I had to keep the vacuum in front of me to hide myself. She posed on the diving board, then dove in head first, and then swam across the short distance to the ladder where I was standing. When she climbed out, her tits were out of her suit. They must have come out from the pressure of the dive and I guess she didn’t notice. I could see her bare tits right in front of me. They looked so neat and firm. They weren’t as big as I thought they were, maybe because the bras had made them look bigger and I was using my imagination too much, but they were a really nice size and I thought they were the nicest ones I had ever seen. She saw me staring and looked down and when she saw her tits were loose, she just said, “Well, I’ll be damned” and then she just pulled her bra cups up over them as if nothing had happened. She stood there and adjusted her tits and her bra right in front of me, then walked around to the diving board and dove again.

When she got to the ladder and climbed out, her tits were out again and when she noticed, all she said was “damn” and started to put them back in and adjust the suit again. It happened a third time but that time she also stopped and tightened the string that tied behind her neck. Her tits popped out like that two more times, and then she asked me to help her tie the strings behind her neck so they would be tighter. I said sure but I was shaking so much I had a hard time. When I was tying the bikini straps, I got to touch her skin and it felt so soft and smooth. I let the straps slip out of my hands once hoping the bra would fall right down but she was holding it onto her tits with her hands.

After I tied the straps, she dove again and the same thing happened. She swore again and said that her damn bathing suit was useless and a nuisance, so if I didn’t mind, she was going to leave the damn top off. I tried to look away and when I next saw her she was walking to the diving board and she didn’t have her bikini top on. Her tits were firm but they jiggled when she walked and they looked so gorgeous. I didn’t know what I was doing about cleaning the pool so I just pretended I did and kept working and watching her when she didn’t think I was looking. After a few more minutes of swimming, she started to dry herself off and it was so neat watching her dry her tits and her legs. Then she put her high heels back on and walked over to the side of the pool that I was now on, but she still didn’t have her top on.

“Here, Robby, let me show you how to do that to make it easier.” She walked over, took the rod from me and proceeded to demonstrate how she wanted it done. The only problem was that she was standing topless right beside me and I was looking at her tits, not at what she was doing. She gave it back to me and told me to try it again. Because I wasn’t watching intently, I didn’t get it right and she moved closer, took my hand and my arm to help me, and when she did, one of her bare tits brushed against my arm. At least, I think it did but I am not sure. Then she said that was good enough for today, and told me to come on in the house when I was finished putting things away.

I put the equipment back in the garage and then I went inside the house. I knocked first and heard her tell me to come in. When I did, she was talking to someone on the phone. She motioned for me to sit down and after I did, I looked over and she was still topless. I heard her ask for an address and a time, and she wrote them down. After a pause, she said yes a couple of times, then told the caller that she couldn’t talk about that on the phone. She said that she would do what the caller wanted and that everything would be fine and that she was sure that the caller would be more than satisfied.

After the call she told me that she had to go to work for a while and that I would have to excuse her in a moment. I asked her what kind of work she did and she said she was an entertainer. I somehow visualized that she was a musician, and for some reason I didn’t say anymore.

She stood up and stopped, then said, “Robby, did it bother you that I took my top off out there?" “No, no, of course not, Mrs. D’Harley.” “I suppose a young good looking young man like you sees a lot of nude girls, don’t you?” “Yeah, sure,” I lied, and then thought it wasn’t a real lie because I did see a lot of them in magazines and on the internet, only not in real life. “Well, I hope I didn’t embarrass you but that damn top just kept slipping off and it was making me mad. I am going to have to return it, I think. What do you think I should do, take it back?” Gee, I don’t know, Mrs. D’Harley, it is sure pretty, I think it looks real neat on you. It’s too bad it doesn’t fit too well.”

What do you like about it, Robby?” That question caught me off guard and I didn’t know what to say. “Well, I just think it looks nice on you, I guess, I’m not sure what it is, but it seems to suit you, I guess.” I somehow stammered. “Thanks for being so honest, Robby, you are sweet and I appreciate it. Anyway, I think I should go and get ready. Will you be back on Thursday?” “Sure, Mrs. D’Harley, Thursday will be fine. I’ll see you then.” “You know Robby, I think perhaps I should give you a key to the garage. My work hours are unpredictable and if I am not here, then you can still do some work if you can get into the garage. If I am not here, the door from the garage to the kitchen is always open so feel free to get a drink from the fridge or to use the washroom if you need to. Just a minute.” Then she went into the kitchen and got a key. She came over a gave it to me and again she was standing topless right in front of me and it didn’t even seem to faze her at all, she just acted so normal. After I took the key and put it in my pocket, I started for the door.

“If you don’t mind, I won’t see you out today,” she said, “seeing as how I’m dressed, I mean undressed.” And she laughed a little and smiled at me. When I turned around to look at her, she was standing up tall on her heels, and she had pulled her shoulders back so that her tits were standing out like bullets and she was staring right at me. I stared at them, smiled sheepishly, and then turned away embarrassed. She said, “You like them, don’t you Robby?” I nodded yes, then she just smiled and said, “Okay, that’s nice, I’ll see you Thursday.” They really were neat. They weren’t huge or anything, but they had such a nice shape and they looked so soft. The brown areas around the nipples were not very big like some of the pictures of other tits that I saw, and her nipples sort of pointed outwards from each other and downwards a little bit too. I could even see some blue veins that ran through them. I just kept staring at them and she just stood there in front of me with her shoulders pulled back and they looked so wonderful. She smiled at me again and finally told me I should probably go since she had an appointment and had to get ready. She said she would see me again in a couple of days.

I closed the door and skipped away down the street, feeling unbelievably light headed. Guess what I did? Yes, I went right to the park again and jerked off, thinking about her tits and remembering what it felt like when one of them brushed against my arm. I jerked off again twice that day and the next day at school and could not take my mind off her. I didn’t learn anything at school and didn’t even want to talk to anyone about anything because I couldn’t keep anything else on my mind but Mrs. D’Harley, I mean Dee Dee. Well, I did think about time and how soon Thursday would come around so I could get back there and see her again, of course.